2-Chloro-4-(5-fluoro-2-methyl-4-nitrophenoxy)pyridine → 4-(2-Chloropyridin-4-yloxy)-2-fluoro-5-methylbenzenamine

HRID 2060679Notes

Reaction equation

HRID 2060679 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[C:13]([F:15])[C:12]([N+:16]([O-])=O)=[CH:11][C:10]=2[CH3:19])[CH:5]=[CH:4][N:3]=1>C(O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:19])=[CH:11][C:12]([NH2:16])=[C:13]([F:15])[CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 866416852-Chloro-4-(5-fluoro-2-methyl-4-nitrophenoxy)pyridine

Product 1

HCID 866243194-(2-Chloropyridin-4-yloxy)-2-fluoro-5-methylbenzenamineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-chloro-4-(5-fluoro-2-methyl-4-nitrophenoxy)pyridine (0.48 g, 1.698 mmol) in ethanol (20 mL) was added Raney Ni (0.4 g). The mixture was stirred under a hydrogen atmosphere (1 atm) overnight at RT. The reaction mixture was filtered through a pad of Celite® and the filtrate was concentrated to obtain the crude 4-(2-chloropyridin-4-yloxy)-2-fluoro-5-methylbenzenamine (assuming a 100% yield).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0fca8b45ecb94ce0affa808a7998d286
Source dataset
uspto-grants-2012_10
Patent number
US08278331B2

Reaction notes

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